
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.
Latest episodes

83 snips
Apr 25, 2025 • 1h 26min
Discord’s Power Move, Slate’s Modular EVs & the “Act for Private Gain” | E2117
Avery Pennarun, CEO of Tailscale, shares insights on revolutionizing VPN technology by simplifying internet networking with innovative solutions. He discusses Tailscale’s impressive growth from 5K to 10K customers and explains how fixing networking issues could ignite the next wave of tech innovation. The conversation also touches on the essential role of data networking for AI companies, the limitations of current cloud services, and the vision for a more decentralized internet architecture, paving the way for future advancements.

115 snips
Apr 23, 2025 • 1h 2min
Cursor’s $300M ARR, Uber’s FTC Battle, and Office Hours with GoShare | E2116
The FTC's lawsuit against Uber raises questions about consumer protection amid subscription management. Cursor's astonishing growth as an AI startup showcases the potential of innovative solutions. Dark patterns in UX design are scrutinized, highlighting the need for transparency. Insights from GoShare's CEO emphasize focus and customer obsession for navigating market turbulence. The discussion also touches on compliance challenges in the gig economy and strategies for startups to adapt and thrive.

94 snips
Apr 21, 2025 • 1h 17min
Robot Lifeguards, TapCheck’s Payday Play & Thalamus’s Wild Market Share | E2115
Join Jason Reminick, Co-founder and CEO of Thalamus, as he dives into a compelling discussion about his platform that expertly matches medical residents with hospitals, boasting an impressive 85% market share. Discover how Thalamus is addressing the U.S. doctor shortage while navigating the complexities of becoming a Public Benefit Corp. The conversation also touches on the challenges of OpenAI's new models, the impact of fintech innovations like TapCheck, and intriguing technology such as robot lifeguards and humanoid races. This is a must-listen for tech and healthcare enthusiasts alike!

114 snips
Apr 18, 2025 • 1h 1min
LMArena Goes Startup, AI App Wars Begin, Scott Bair’s Design Playbook | E2114
In this engaging discussion, Scott Bair, Director of Strategy for Lunor, shares his expertise in branding and design for startups. He offers actionable tips on logo creation, emphasizing color theory's emotional impact. The conversation also dives into the rise of LMArena, a competitive AI leaderboard, and the changing monetization strategies in tech, highlighting the significance of user engagement for startups. Additionally, the dynamic landscape of AI acquisitions and emerging application-layer AI startups are examined, making for a thought-provoking listen.

140 snips
Apr 17, 2025 • 25min
AI Progress and Impact on Ecosystem Players with CapitalG’s Jill Chase | AI Basics with Google Cloud
Jill Chase, a Partner at CapitalG, dives into how AI is transforming the startup ecosystem. With insights from successful companies like Motif and Abridge, she highlights the importance of durability in product offerings, emphasizing that speed alone isn't enough. Jill discusses practical AI applications in business operations, the evolution from copilots to autonomous agents, and the need for unique user experiences in a competitive market. For founders and investors in AI, her insights present a roadmap to navigate the challenges ahead.

91 snips
Apr 17, 2025 • 1h 7min
Cuts CEO Talks Tariffs, Figma's IPO Buzz, and a Nerd Crawler Update | E2113
Steven Borrelli, CEO of Cuts Clothing and e-commerce expert, discusses the unsettling impact of tariffs on his business and the larger retail landscape. He shares insights on how these policies affect supply chains and pricing, urging a focus on American craftsmanship. The conversation shifts to the recent buzz around Figma's IPO and the competitive dynamics shaping the tech market. Borrelli also touches on the challenges e-commerce faces amidst a changing economic environment, highlighting the necessity for startups to adapt strategically.

107 snips
Apr 15, 2025 • 1h 8min
Vertical AI Innovations: Abacus LLM in Finance & Synthesia's Video Avatars | E2112
David Moscatelli, founder of Abacus, specializes in bringing generative AI to the finance sector, focusing on data control and accuracy for banks. Victor Riparbelli, CEO of Synthesia, leads an AI platform transforming corporate documents into engaging videos. They discuss the unique challenges of implementing AI in regulated industries and how on-prem LLMs enhance data management. Additionally, they explore the rise of customizable AI avatars that streamline communication for enterprises and the critical balance of ethics in AI development.

86 snips
Apr 15, 2025 • 1h 3min
HuggingFace Buys Pollen Robotics, DHH & Bezos Founder Advice & a JCal Origin Story | E2111
The latest discussion ignites excitement over Blue Origin's all-female crew mission and what it means for space tourism. Hugging Face's surprising acquisition of Pollen Robotics sparks debates about AI's role in real-world applications. Jack Dorsey's controversial views on intellectual property laws fuel heated discussions. Meanwhile, the staggering $39 billion valuation of Figure AI raises eyebrows, highlighting the unpredictable landscape of startup investments and the importance of navigating their inherent risks.

82 snips
Apr 12, 2025 • 1h 9min
Palantir's Fellowship, Coco Robots & Startup Office Hours | E2110
In this discussion, Brian Watson, the founder of InviteJet and a graduate of the LA 33 accelerator, shares insights on innovative calendar marketing tools. They delve into Palantir’s new fellowship program, which challenges traditional education paths for tech talent. The conversation also touches on DoorDash's partnership with Coco robots for food delivery in urban settings. Plus, practical strategies for startups on acquiring their first customers and a wild cautionary tale involving an AI deepfake investor. A wealth of actionable advice awaits!

48 snips
Apr 10, 2025 • 1h 7min
70mph Drone Deliveries, 125% Tariffs & What $10M Exits Really Mean | E2109
Sergie Poe, CEO of Orchestra, a communication software company, shares insights on navigating today's startup landscape. He discusses the rise of 70mph drone deliveries in Dallas and their potential impact on logistics. The conversation then dives into the implications of Trump's 125% tariff on China, warning founders about possible layoffs and bankruptcies. Sergie also highlights the risks posed by small startup exits, where founders walk away with significant sums, influencing their future funding needs.