This Week in Startups

Jason Calacanis
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55 snips
Dec 4, 2025 • 57min

Getting past the “Cardinal Sins of Delegating” with Jonathan Swanson of Athena | E2218

Jonathan Swanson, Founder and CEO of Athena, shares insights on delegating effectively to reclaim time for busy executives. He discusses transitioning from Thumbtack to Athena, emphasizing the importance of pairing human assistants with AI support. Jonathan reveals the concept of 'Black Diamond Delegating' and the gains from managing multiple specialized executive assistants. They explore the significance of checklists and playbooks in maximizing productivity, and Jonathan offers tips for hiring assistants, even starting with DIY options like ChatGPT.
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24 snips
Dec 3, 2025 • 1h 26min

Monumental Makes Construction Bots Play Nice Together | E2217

Join Salar al Khafaji, CEO of Monumental, who’s revolutionizing construction with autonomous bricklaying robots, addressing labor shortages and enhancing site logistics. He discusses the importance of creating distinct operation zones for robots and the complexities of navigating European fundraising. Mike Flanigan, CEO of Seasats, dives into designing autonomous ocean drones, focusing on the challenges of sourcing components and ensuring operational efficiency. Together, they explore innovative solutions that tackle real-world problems in construction and maritime tech.
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70 snips
Dec 2, 2025 • 58min

Is $MSTR over? Jason takes his victory lap. | E2216

The discussion dives into the struggles of MicroStrategy's Bitcoin strategy and questions the value of its convoluted financial schemes. Jason outlines four red flags to watch out for in investments, emphasizing simplicity over complexity. The show also covers Tether's recent downgrade by S&P Global and the need for stronger audits in the crypto space. With robot vacuums and humanoid robots on the radar, the hosts explore the potential for AI in everyday life, all while Jason takes a victory lap for predicting MicroStrategy's decline.
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46 snips
Nov 26, 2025 • 1h 16min

SO MANY THINGS need to go right just so you can watch a TikTok! | E2215

Gou Rao, CEO of Neubird, reveals the incredible layers involved in delivering a simple TikTok video and how their AI, Hawkeye, acts as an agentic system to streamline IT operations. He highlights the complexities engineers face and the efficiency gains from AI-driven diagnostics. Meanwhile, Michael Vilardo, CEO of Subject AI, discusses how gamification in educational tech engages students and personalizes learning, along with AI tools that ease teachers' workloads. It's a fascinating dive into the intersection of AI with tech and education!
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36 snips
Nov 24, 2025 • 52min

Even great startups sometimes need to pivot (feat. Francisco Cornejo of Theo) | E2214

Francisco Cornejo, founder of Familify and the innovative Theo app, discusses a pivotal moment when Storybook's growth stalled despite great reviews. By experimenting with Bible stories, they discovered strong user demand that propelled Theo to surpass Storybook in just weeks. Colin Sebastian introduces En Vérité, highlighting how AI simplifies due diligence for investors, while Jake Triton of Pitch Perfect shares insights on SMS compliance and how his platform enhances communication for SMBs. The conversation emphasizes adaptability and data-driven decisions for startup success.
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104 snips
Nov 22, 2025 • 56min

Jason predicts a “major M&A moment” in the next six months! | E2213

The discussion kicks off with Jason predicting a wave of major mergers and acquisitions ahead. They delve into the evolving landscape of AI, highlighting Google's impressive consumer adoption metrics. The duo debates Nvidia's strong performance and the uncertainty surrounding its deals with OpenAI. They also explore how restaurants are becoming new intellectual property and share insights on global startup expansion. Plus, a comparison of AI tools shows Google's impressive infographic generation. Buckle up for an engaging ride through the startup world!
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67 snips
Nov 20, 2025 • 1h 5min

Why data is the biggest AI bottleneck (feat. Arthur Mensch of Mistral AI) | E2212

Arthur Mensch, Co-founder and CEO of Mistral AI, dives into the real bottleneck for AI progress: a shortage of data. He discusses how enterprises can enhance the value of their AI initiatives and why Mistral's mission is to empower users to be independent. Mensch also explores the difference between open-source and closed models, warning against over-optimizing benchmarks for AI. With insights on robotics and the regulatory landscape in Europe, he reveals the challenges of building effective AI applications in today's fast-paced environment.
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66 snips
Nov 19, 2025 • 47min

AI Model Showdown: Grok 4.1 vs. Gemini 3 | E2211

This discussion dives into the fierce competition between AI models Grok 4.1 and Gemini 3, exploring their potential to shake off the prevailing pessimism in the tech industry. The hosts dissect a recent Cloudflare outage, contemplating the implications for startups when their services go offline. They also predict a future where businesses run their own models locally, balancing data privacy with tech accessibility. The episode wraps up with insights on market reactions to these AI developments and the ongoing risks of job displacement due to automation.
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43 snips
Nov 18, 2025 • 1h 14min

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

The discussion kicks off with Archer's ambitious acquisition of an airport and Joby's moves in eVTOL. Jason shares insights from his travels to MENA and Japan, highlighting booming construction and fintech sectors. Ramp's $300M fundraising round sparks talk about AI making corporate finance smarter. A quirky tale about KitKat, the bodega cat, raises eyebrows after a Waymo incident. The conversation also dives into the potential of AI in reshaping work and the implications of Jeff Bezos returning to lead an AI-focused initiative.
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59 snips
Nov 14, 2025 • 1h 14min

Stop ghosting your friends with Nox’s RPLY, plus Alloy Automation and a Shopify flashback | E2209

Molly Cantillon, Founder of Nox, discusses her innovative app RPLY, designed to help users manage their messaging and achieve inbox zero. She dives into how RPLY leverages AI to map user relationships and organize communication. Greg Mojica, CEO of Alloy Automation, shares insights on AI agents and the often misunderstood need for human escalation in workflows. The conversation touches on the current limitations of AI and how they can enhance relationship management while keeping meaningful interactions human. A nostalgic flashback to Shopify's early days completes the show.

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