

This Week in Startups
Jason Calacanis
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
Mentioned books

9 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.

29 snips
Nov 13, 2025 • 1h 14min
Why We Need Ferries and Tugboats in Space w/ Orbital Operations | E2208
Ben Schleuniger, co-founder and CEO of Orbital Operations, discusses groundbreaking advancements in space logistics. He highlights the challenges of moving satellites in increasingly crowded orbits and the critical need for mobility in space. With their innovative cryogenic orbital maneuvering vehicles, like Astraeus, they're tackling space refueling and transportation. Ben also shares insights on the future of reusable rockets, the importance of active refrigeration systems, and the rising demand for commercial space solutions amidst growing defense interests.

61 snips
Nov 11, 2025 • 1h 3min
Inside Harvey AI’s $8 billion AI lawyer app, PLUS How OpenRouter unites the LLMs | E2207
Gabe Pereyra, Co-founder and President of Harvey AI, discusses how AI can revolutionize the legal industry, overcoming challenges posed by traditional billable hours. He highlights the success of Harvey’s Vault and Assistant products and shares insights on client collaboration. Alex Atallah, Co-founder and CEO of OpenRouter, delves into the complexities of integrating multiple LLMs with a unified API, emphasizing the growing importance of benchmarks and resource-specific models. Both guests explore the transformative impact of AI on professional services.

99 snips
Nov 10, 2025 • 1h 5min
IPO Mania hits the TWiST 500! Three companies are ready to go public | E2206
Three startups are preparing for IPOs, highlighting the booming cybersecurity sector. Controversy unfolds as Marc Andreessen takes on the Pope over AI ethics. Discussion shifts to the potential impact of AI on job displacement and whether it could spark a surge in new businesses. Allegations involving Giga raise questions about startup culture and management. Meanwhile, Mercury, Ledger, and 1Password show strong growth and readiness for public markets, while Gamma makes strides in AI with impressive user numbers.

66 snips
Nov 8, 2025 • 1h 15min
It’s a boat, it’s a plane, it’s REGENT’s Seafarer | E2205
Billy Thalheimer, founder of REGENT, reveals their innovative Seaglider, a hybrid air-and-sea vehicle poised to revolutionize travel while minimizing airport hassles. Ayaan Parekh of Convexia shares insights on leveraging AI to discover and repurpose shelved drug candidates for rare diseases. Finally, Hunter Leath from Arkyl discusses their caching-as-a-service solution that transforms cloud data access into a local experience, speeding up applications while reducing costs. The future of transport and healthcare technology is fresh and promising!

69 snips
Nov 6, 2025 • 1h 24min
Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204
Deedy Das, a Partner at Menlo Ventures known for his focus on product-led growth and AI, and Jay Eum, a General Partner at GFT Ventures specializing in frontier tech investments, dive into the complexities of the current venture landscape. They discuss the surprising rise in early-stage AI funding and the transition in investor strategies. The duo tackles the challenges of raising private capital before IPOs and debates whether increased funding truly leads to more great companies. They also explore the difficulty of being both a founder and an investor in today's market.

71 snips
Nov 3, 2025 • 1h 18min
Sending datacenters into orbit | E2203
Lon Harris, an editorial director and media commentator, dives into exciting discussions on the potential of AI-powered datacenters in orbit. He explores the implications of StarCloud's recent launch and whether Wi-Fi really works in space. The conversation shifts to Netflix's interest in Warner Bros, with insights on how acquiring CNN could transform their news strategy. Plus, there's a fun segment on favorite Nazi hunter films, revealing how storytelling uses villains for deeper narratives. A blend of industry insight and entertaining anecdotes!

70 snips
Nov 1, 2025 • 1h 19min
What will be OpenAI’s IPO price? Place ya bets! | E2202
Oliver, the show's producer and tech guru, joins the discussion to unveil the Suno AI music app, showcasing its potential to create music using prompts. The hosts explore the implications of OpenAI's IPO, betting on its future valuation, while also analyzing Amazon's stock for the next five years. Oliver also demonstrates how to generate unique songs, editing tracks like a pro. They dive into legal risks in tech and the competitive landscape of startups building their own models, all while sharing insights on the evolving music industry.

95 snips
Oct 30, 2025 • 1h 39min
Grammarly is now Superhuman! CEO Shishir Mehrotra explains the rebrand | E2201
In this discussion, Shishir Mehrotra, the innovative CEO transitioning Grammarly into Superhuman, shares insights on the ambitious rebrand. He explains why a name change is pivotal for broadening the company’s vision. Shishir unveils Superhuman Go, an AI assistant designed to seamlessly integrate into daily workflows. He dives into their strategy for developing adaptable agents that empower users while addressing AI’s impact on jobs. Plus, he discusses privacy measures and the pricing model for their new product suite, emphasizing user-centric design.

57 snips
Oct 29, 2025 • 1h 19min
iPhone Air is “inspiring,” and a first step toward Apple Glasses (w/ Zach Handshoe of SpatialGen) | E2200
Zachary Handshoe, Co-founder of SpatialGen, discusses the thrill and pressure of presenting at Apple's immersive media event while showcasing their platform for spatial video infrastructure. Raiza Martin, Co-founder of Huxe, dives into how their audio-forward AI app enhances personalization and user retention, focusing on audio consumption habits. Lastly, Chess Grandmaster Vasif Durarbayli pitches ChessEver, a pro-grade app designed for serious chess players, highlighting its comprehensive event coverage and unique analysis features.


